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Literature summary extracted from

  • Pedgaonkar, G.; Sridevi, J.; Jeankumar, V.; Saxena, S.; Devi, P.; Renuka, J.; Yogeeswari, P.; Sriram, D.
    Development of 2-(4-oxoquinazolin-3(4H)-yl)acetamide derivatives as novel enoyl-acyl carrier protein reductase (InhA) inhibitors for the treatment of tuberculosis (2014), Eur. J. Med. Chem., 86, 613-627 .
    View publication on PubMed

Application

EC Number Application Comment Organism
1.3.1.9 pharmacology the enzyme is a target for developing novel anti-tubercular agents Mycobacterium tuberculosis
1.3.1.118 pharmacology the enzyme is a target for developing novel anti-tubercular agents Mycobacterium tuberculosis

Cloned(Commentary)

EC Number Cloned (Comment) Organism
1.3.1.9 expression in Escherichia coli BL21 (DE3) Mycobacterium tuberculosis
1.3.1.118 expression in Escherichia coli BL21 (DE3) Mycobacterium tuberculosis

Inhibitors

EC Number Inhibitors Comment Organism Structure
1.3.1.9 2-(2-methyl-4-oxoquinazolin-3(4H)-yl)-N-(5-nitrothiazol-2-yl)acetamide
-
 Mycobacterium tuberculosis
1.3.1.9 2-(2-methyl-4-oxoquinazolin-3(4H)-yl)-N-(6-nitrobenzo[d]thiazol-2-yl)acetamide
-
 Mycobacterium tuberculosis
1.3.1.9 2-(2-methyl-4-oxoquinazolin-3(4H)-yl)-N-(thiophen-2-ylmethyl)acetamide
-
 Mycobacterium tuberculosis
1.3.1.9 2-(2-methyl-4-oxoquinazolin-3(4H)-yl)-N-phenylacetamide
-
 Mycobacterium tuberculosis
1.3.1.9 2-(4-oxoquinazolin-3(4H)-yl)-N-(thiophen-2-ylmethyl)acetamide
-
 Mycobacterium tuberculosis
1.3.1.9 2-(4-oxoquinazolin-3(4H)-yl)-N-phenylacetamide
-
 Mycobacterium tuberculosis
1.3.1.9 2-(6-chloro-2-methyl-4-oxoquinazolin-3(4H)-yl)-N-(2-chloro-5-(trifluoromethyl)phenyl)acetamide
-
 Mycobacterium tuberculosis
1.3.1.9 2-(6-chloro-2-methyl-4-oxoquinazolin-3(4H)-yl)-N-(5-nitrothiazol-2-yl)acetamide
-
 Mycobacterium tuberculosis
1.3.1.9 2-(6-chloro-2-methyl-4-oxoquinazolin-3(4H)-yl)-N-(6-nitrobenzo[d]thiazol-2-yl)acetamide
-
 Mycobacterium tuberculosis
1.3.1.9 2-(6-chloro-2-methyl-4-oxoquinazolin-3(4H)-yl)-N-(furan-2-ylmethyl)acetamide
-
 Mycobacterium tuberculosis
1.3.1.9 2-(6-chloro-2-methyl-4-oxoquinazolin-3(4H)-yl)-N-(thiophen-2-ylmethyl)acetamide
-
 Mycobacterium tuberculosis
1.3.1.9 2-(6-chloro-2-methyl-4-oxoquinazolin-3(4H)-yl)-N-phenylacetamide
-
 Mycobacterium tuberculosis
1.3.1.9 2-(6-chloro-4-oxoquinazolin-3(4H)-yl)-N-(2-chloro-5-(trifluoromethyl)phenyl)acetamide
-
 Mycobacterium tuberculosis
1.3.1.9 2-(6-chloro-4-oxoquinazolin-3(4H)-yl)-N-(5-nitrothiazol-2-yl)acetamide
-
 Mycobacterium tuberculosis
1.3.1.9 2-(6-chloro-4-oxoquinazolin-3(4H)-yl)-N-(6-nitrobenzo[d]thiazol-2-yl)acetamide
-
 Mycobacterium tuberculosis
1.3.1.9 2-(6-chloro-4-oxoquinazolin-3(4H)-yl)-N-(furan-2-ylmethyl)acetamide
-
 Mycobacterium tuberculosis
1.3.1.9 2-(6-chloro-4-oxoquinazolin-3(4H)-yl)-N-(thiophen-2-ylmethyl)acetamide
-
 Mycobacterium tuberculosis
1.3.1.9 2-(6-chloro-4-oxoquinazolin-3(4H)-yl)-N-phenylacetamide
-
 Mycobacterium tuberculosis
1.3.1.9 additional information 28 2-(4-oxoquinazolin-3(4H)-yl)acetamide derivatives are synthesized and evaluated for their in vitro Mycobacterium tuberculosis InhA inhibition. Compounds are evaluated for their in vitro activity against drug sensitive and resistant Mycobacterium tuberculosis strains and cytotoxicity against RAW 264.7 cell line. Compounds are docked at the active site of InhA to understand their binding mode and differential scanning fluorimetry is performed to ascertain their protein interaction and stability Mycobacterium tuberculosis
1.3.1.9 N-(2-chloro-5-(trifluoromethyl)phenyl)-2-(2-methyl-4-oxoquinazolin-3(4H)-yl)acetamide
-
 Mycobacterium tuberculosis
1.3.1.9 N-(2-chloro-5-(trifluoromethyl)phenyl)-2-(4-oxoquinazolin-3(4H)-yl)acetamide
-
 Mycobacterium tuberculosis
1.3.1.9 N-(5-nitrothiazol-2-yl)-2-(4-oxoquinazolin-3(4H)-yl)acetamide
-
 Mycobacterium tuberculosis
1.3.1.9 N-(6-nitrobenzo[d]thiazol-2-yl)-2-(4-oxoquinazolin-3(4H)-yl)acetamide
-
 Mycobacterium tuberculosis
1.3.1.9 N-(benzo[d]thiazol-2-yl)-2-(2-methyl-4-oxoquinazolin-3(4H)-yl)acetamide
-
 Mycobacterium tuberculosis
1.3.1.9 N-(benzo[d]thiazol-2-yl)-2-(4-oxoquinazolin-3(4H)-yl)acetamide
-
 Mycobacterium tuberculosis
1.3.1.9 N-(benzo[d]thiazol-2-yl)-2-(6-chloro-2-methyl-4-oxoquinazolin-3(4H)-yl)acetamide
-
 Mycobacterium tuberculosis
1.3.1.9 N-(furan-2-yl-methyl)-2-(4-oxoquinazolin-3(4H)-yl)acetamide
-
 Mycobacterium tuberculosis
1.3.1.9 N-(furan-2-ylmethyl)-2-(2-methyl-4-oxoquinazolin-3(4H)-yl)acetamide
-
 Mycobacterium tuberculosis
1.3.1.118 2-(2-methyl-4-oxoquinazolin-3(4H)-yl)-N-(5-nitrothiazol-2-yl)acetamide
-
 Mycobacterium tuberculosis
1.3.1.118 2-(2-methyl-4-oxoquinazolin-3(4H)-yl)-N-(6-nitrobenzo[d]thiazol-2-yl)acetamide
-
 Mycobacterium tuberculosis
1.3.1.118 2-(2-methyl-4-oxoquinazolin-3(4H)-yl)-N-(thiophen-2-ylmethyl)acetamide
-
 Mycobacterium tuberculosis
1.3.1.118 2-(2-methyl-4-oxoquinazolin-3(4H)-yl)-N-phenylacetamide
-
 Mycobacterium tuberculosis
1.3.1.118 2-(4-oxoquinazolin-3(4H)-yl)-N-(thiophen-2-ylmethyl)acetamide
-
 Mycobacterium tuberculosis
1.3.1.118 2-(4-oxoquinazolin-3(4H)-yl)-N-phenylacetamide
-
 Mycobacterium tuberculosis
1.3.1.118 2-(6-chloro-2-methyl-4-oxoquinazolin-3(4H)-yl)-N-(2-chloro-5-(trifluoromethyl)phenyl)acetamide
-
 Mycobacterium tuberculosis
1.3.1.118 2-(6-chloro-2-methyl-4-oxoquinazolin-3(4H)-yl)-N-(5-nitrothiazol-2-yl)acetamide
-
 Mycobacterium tuberculosis
1.3.1.118 2-(6-chloro-2-methyl-4-oxoquinazolin-3(4H)-yl)-N-(6-nitrobenzo[d]thiazol-2-yl)acetamide
-
 Mycobacterium tuberculosis
1.3.1.118 2-(6-chloro-2-methyl-4-oxoquinazolin-3(4H)-yl)-N-(furan-2-ylmethyl)acetamide
-
 Mycobacterium tuberculosis
1.3.1.118 2-(6-chloro-2-methyl-4-oxoquinazolin-3(4H)-yl)-N-(thiophen-2-ylmethyl)acetamide
-
 Mycobacterium tuberculosis
1.3.1.118 2-(6-chloro-2-methyl-4-oxoquinazolin-3(4H)-yl)-N-phenylacetamide
-
 Mycobacterium tuberculosis
1.3.1.118 2-(6-chloro-4-oxoquinazolin-3(4H)-yl)-N-(2-chloro-5-(trifluoromethyl)phenyl)acetamide
-
 Mycobacterium tuberculosis
1.3.1.118 2-(6-chloro-4-oxoquinazolin-3(4H)-yl)-N-(5-nitrothiazol-2-yl)acetamide
-
 Mycobacterium tuberculosis
1.3.1.118 2-(6-chloro-4-oxoquinazolin-3(4H)-yl)-N-(6-nitrobenzo[d]thiazol-2-yl)acetamide
-
 Mycobacterium tuberculosis
1.3.1.118 2-(6-chloro-4-oxoquinazolin-3(4H)-yl)-N-(furan-2-ylmethyl)acetamide
-
 Mycobacterium tuberculosis
1.3.1.118 2-(6-chloro-4-oxoquinazolin-3(4H)-yl)-N-(thiophen-2-ylmethyl)acetamide
-
 Mycobacterium tuberculosis
1.3.1.118 2-(6-chloro-4-oxoquinazolin-3(4H)-yl)-N-phenylacetamide
-
 Mycobacterium tuberculosis
1.3.1.118 additional information twenty eight 2-(4-oxoquinazolin-3(4H)-yl)acetamide derivatives are synthesized and evaluated for their in vitro Mycobacterium tuberculosis InhA inhibition. Compounds are evaluated for their in vitro activity against drug sensitive and resistant Mycobacterium tuberculosis strains and cytotoxicity against RAW 264.7 cell line. Compounds are docked at the active site of InhA to understand their binding mode and differential scanning fluorimetry is performed to ascertain their protein interaction and stability Mycobacterium tuberculosis
1.3.1.118 N-(2-chloro-5-(trifluoromethyl)phenyl)-2-(2-methyl-4-oxoquinazolin-3(4H)-yl)acetamide
-
 Mycobacterium tuberculosis
1.3.1.118 N-(2-chloro-5-(trifluoromethyl)phenyl)-2-(4-oxoquinazolin-3(4H)-yl)acetamide
-
 Mycobacterium tuberculosis
1.3.1.118 N-(5-nitrothiazol-2-yl)-2-(4-oxoquinazolin-3(4H)-yl)acetamide
-
 Mycobacterium tuberculosis
1.3.1.118 N-(6-nitrobenzo[d]thiazol-2-yl)-2-(4-oxoquinazolin-3(4H)-yl)acetamide
-
 Mycobacterium tuberculosis
1.3.1.118 N-(benzo[d]thiazol-2-yl)-2-(2-methyl-4-oxoquinazolin-3(4H)-yl)acetamide
-
 Mycobacterium tuberculosis
1.3.1.118 N-(benzo[d]thiazol-2-yl)-2-(4-oxoquinazolin-3(4H)-yl)acetamide
-
 Mycobacterium tuberculosis
1.3.1.118 N-(benzo[d]thiazol-2-yl)-2-(6-chloro-2-methyl-4-oxoquinazolin-3(4H)-yl)acetamide
-
 Mycobacterium tuberculosis
1.3.1.118 N-(furan-2-yl-methyl)-2-(4-oxoquinazolin-3(4H)-yl)acetamide
-
 Mycobacterium tuberculosis
1.3.1.118 N-(furan-2-ylmethyl)-2-(2-methyl-4-oxoquinazolin-3(4H)-yl)acetamide
-
 Mycobacterium tuberculosis

Organism

EC Number Organism UniProt Comment Textmining
1.3.1.9 Mycobacterium tuberculosis P9WGR1
-
-
1.3.1.9 Mycobacterium tuberculosis ATCC 25618 P9WGR1
-
-
1.3.1.118 Mycobacterium tuberculosis P9WGR1
-
-
1.3.1.118 Mycobacterium tuberculosis ATCC 25618 P9WGR1
-
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.3.1.9 trans-2-decenoyl-CoA + NADH + H+
-
 Mycobacterium tuberculosis decanoyl-CoA + NAD+
-
 ?
1.3.1.9 trans-2-decenoyl-CoA + NADH + H+
-
 Mycobacterium tuberculosis ATCC 25618 decanoyl-CoA + NAD+
-
 ?
1.3.1.118 trans-2-decenoyl-CoA + NADH + H+
-
 Mycobacterium tuberculosis decanoyl-CoA + NAD+
-
 ?
1.3.1.118 trans-2-decenoyl-CoA + NADH + H+
-
 Mycobacterium tuberculosis ATCC 25618 decanoyl-CoA + NAD+
-
 ?

Synonyms

EC Number Synonyms Comment Organism
1.3.1.9 enoyl acyl carrier protein reductase
-
 Mycobacterium tuberculosis
1.3.1.9 InhA
-
 Mycobacterium tuberculosis
1.3.1.118 enoyl acyl carrier protein reductase
-
 Mycobacterium tuberculosis
1.3.1.118 InhA
-
 Mycobacterium tuberculosis

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
1.3.1.9 25
-
 assay at Mycobacterium tuberculosis
1.3.1.118 25
-
 assay at Mycobacterium tuberculosis

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
1.3.1.9 6.8
-
 assay at Mycobacterium tuberculosis
1.3.1.118 6.8
-
 assay at Mycobacterium tuberculosis

IC50 Value

EC Number IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
1.3.1.9 0.00312
-
 pH 6.8, 25°C Mycobacterium tuberculosis 2-(6-chloro-4-oxoquinazolin-3(4H)-yl)-N-(furan-2-ylmethyl)acetamide
1.3.1.9 0.00312
-
 pH 6.8, 25°C Mycobacterium tuberculosis 2-(6-chloro-2-methyl-4-oxoquinazolin-3(4H)-yl)-N-phenylacetamide
1.3.1.9 0.00452
-
 pH 6.8, 25°C Mycobacterium tuberculosis 2-(6-chloro-2-methyl-4-oxoquinazolin-3(4H)-yl)-N-(furan-2-ylmethyl)acetamide
1.3.1.9 0.00456
-
 pH 6.8, 25°C Mycobacterium tuberculosis 2-(6-chloro-4-oxoquinazolin-3(4H)-yl)-N-(2-chloro-5-(trifluoromethyl)phenyl)acetamide
1.3.1.9 0.00512
-
 pH 6.8, 25°C Mycobacterium tuberculosis N-(6-nitrobenzo[d]thiazol-2-yl)-2-(4-oxoquinazolin-3(4H)-yl)acetamide
1.3.1.9 0.00601
-
 pH 6.8, 25°C Mycobacterium tuberculosis 2-(2-methyl-4-oxoquinazolin-3(4H)-yl)-N-(thiophen-2-ylmethyl)acetamide
1.3.1.9 0.00616
-
 pH 6.8, 25°C Mycobacterium tuberculosis 2-(2-methyl-4-oxoquinazolin-3(4H)-yl)-N-(6-nitrobenzo[d]thiazol-2-yl)acetamide
1.3.1.9 0.00676
-
 pH 6.8, 25°C Mycobacterium tuberculosis 2-(6-chloro-2-methyl-4-oxoquinazolin-3(4H)-yl)-N-(thiophen-2-ylmethyl)acetamide
1.3.1.9 0.00686
-
 pH 6.8, 25°C Mycobacterium tuberculosis N-(furan-2-ylmethyl)-2-(2-methyl-4-oxoquinazolin-3(4H)-yl)acetamide
1.3.1.9 0.00712
-
 pH 6.8, 25°C Mycobacterium tuberculosis 2-(6-chloro-4-oxoquinazolin-3(4H)-yl)-N-(thiophen-2-ylmethyl)acetamide
1.3.1.9 0.00716
-
 pH 6.8, 25°C Mycobacterium tuberculosis 2-(6-chloro-2-methyl-4-oxoquinazolin-3(4H)-yl)-N-(2-chloro-5-(trifluoromethyl)phenyl)acetamide
1.3.1.9 0.00778
-
 pH 6.8, 25°C Mycobacterium tuberculosis 2-(6-chloro-4-oxoquinazolin-3(4H)-yl)-N-phenylacetamide
1.3.1.9 0.00816
-
 pH 6.8, 25°C Mycobacterium tuberculosis N-(2-chloro-5-(trifluoromethyl)phenyl)-2-(4-oxoquinazolin-3(4H)-yl)acetamide
1.3.1.9 0.00836
-
 pH 6.8, 25°C Mycobacterium tuberculosis N-(benzo[d]thiazol-2-yl)-2-(6-chloro-2-methyl-4-oxoquinazolin-3(4H)-yl)acetamide
1.3.1.9 0.00892
-
 pH 6.8, 25°C Mycobacterium tuberculosis 2-(2-methyl-4-oxoquinazolin-3(4H)-yl)-N-phenylacetamide
1.3.1.9 0.00906
-
 pH 6.8, 25°C Mycobacterium tuberculosis N-(2-chloro-5-(trifluoromethyl)phenyl)-2-(2-methyl-4-oxoquinazolin-3(4H)-yl)acetamide
1.3.1.118 0.00312
-
 pH 6.8, 25°C Mycobacterium tuberculosis 2-(6-chloro-4-oxoquinazolin-3(4H)-yl)-N-(furan-2-ylmethyl)acetamide
1.3.1.118 0.00312
-
 pH 6.8, 25°C Mycobacterium tuberculosis 2-(6-chloro-2-methyl-4-oxoquinazolin-3(4H)-yl)-N-phenylacetamide
1.3.1.118 0.00452
-
 pH 6.8, 25°C Mycobacterium tuberculosis 2-(6-chloro-2-methyl-4-oxoquinazolin-3(4H)-yl)-N-(furan-2-ylmethyl)acetamide
1.3.1.118 0.00456
-
 pH 6.8, 25°C Mycobacterium tuberculosis 2-(6-chloro-4-oxoquinazolin-3(4H)-yl)-N-(2-chloro-5-(trifluoromethyl)phenyl)acetamide
1.3.1.118 0.00512
-
 pH 6.8, 25°C Mycobacterium tuberculosis N-(6-nitrobenzo[d]thiazol-2-yl)-2-(4-oxoquinazolin-3(4H)-yl)acetamide
1.3.1.118 0.00601
-
 pH 6.8, 25°C Mycobacterium tuberculosis 2-(2-methyl-4-oxoquinazolin-3(4H)-yl)-N-(thiophen-2-ylmethyl)acetamide
1.3.1.118 0.00616
-
 pH 6.8, 25°C Mycobacterium tuberculosis 2-(2-methyl-4-oxoquinazolin-3(4H)-yl)-N-(6-nitrobenzo[d]thiazol-2-yl)acetamide
1.3.1.118 0.00676
-
 pH 6.8, 25°C Mycobacterium tuberculosis 2-(6-chloro-2-methyl-4-oxoquinazolin-3(4H)-yl)-N-(thiophen-2-ylmethyl)acetamide
1.3.1.118 0.00686
-
 pH 6.8, 25°C Mycobacterium tuberculosis N-(furan-2-ylmethyl)-2-(2-methyl-4-oxoquinazolin-3(4H)-yl)acetamide
1.3.1.118 0.00712
-
 pH 6.8, 25°C Mycobacterium tuberculosis 2-(6-chloro-4-oxoquinazolin-3(4H)-yl)-N-(thiophen-2-ylmethyl)acetamide
1.3.1.118 0.00716
-
 pH 6.8, 25°C Mycobacterium tuberculosis 2-(6-chloro-2-methyl-4-oxoquinazolin-3(4H)-yl)-N-(2-chloro-5-(trifluoromethyl)phenyl)acetamide
1.3.1.118 0.00778
-
 pH 6.8, 25°C Mycobacterium tuberculosis 2-(6-chloro-4-oxoquinazolin-3(4H)-yl)-N-phenylacetamide
1.3.1.118 0.00816
-
 pH 6.8, 25°C Mycobacterium tuberculosis N-(2-chloro-5-(trifluoromethyl)phenyl)-2-(4-oxoquinazolin-3(4H)-yl)acetamide
1.3.1.118 0.00836
-
 pH 6.8, 25°C Mycobacterium tuberculosis N-(benzo[d]thiazol-2-yl)-2-(6-chloro-2-methyl-4-oxoquinazolin-3(4H)-yl)acetamide
1.3.1.118 0.00892
-
 pH 6.8, 25°C Mycobacterium tuberculosis 2-(2-methyl-4-oxoquinazolin-3(4H)-yl)-N-phenylacetamide
1.3.1.118 0.00906
-
 pH 6.8, 25°C Mycobacterium tuberculosis N-(2-chloro-5-(trifluoromethyl)phenyl)-2-(2-methyl-4-oxoquinazolin-3(4H)-yl)acetamide